MLB pitcher leaves spring training to coach high school basketball team at state tournament

Veteran St. Louis Cardinals pitcher receives special permission from MLB team to leave spring training, help Oregon high school team win trophy

Keynan Middleton needed to finish what he started with the Putnam boys basketball team. 

Middleton, a relief pitcher for the St. Louis Cardinals, began running the Kingsmen’s morning workouts in October and spent the first two-plus months of the regular season on the bench as an assistant to head coach Ali Mihub.

The gig was slated to end when Middleton left for spring training near the conclusion of Northwest Oregon Conference play, but the Cardinals made a promise to the eighth-year MLB veteran: If Putnam qualified for the 5A state tournament and Middleton wasn’t slated to throw during those dates, he could return to Oregon and help the team attempt to earn its first trophy since 1990. 

The Kingsmen punched their ticket to Linfield University with a state round-of-16 win over South Albany and erased a 17-point deficit in a March 6 quarterfinal to stun North Eugene in overtime, 61-57. One day later, Middleton threw an inning of scoreless relief against the Houston Astros. He was on a plane from Florida to Oregon shortly thereafter. 

Putnam wound up placing fifth after consecutive losses to Wilsonville and Woodburn, but Middleton was thrilled to complete the journey he began back in October.

“Everybody kind of knows my background there at Spring Training,” Middleton said. “A lot of people asked me about the coaching, and once I told them that we had playoff games, they told me if I wasn’t throwing in the next few days, I could head back. And they fulfilled that promise, and it was something to enjoy.

“I was there for all of our good days during the season, so I’m glad I got to be here for the bad ones, too, to be able to talk them through it and help them learn from it.”

Mihub, Putnam’s first-year head coach, said Middleton’s return provided a morale boost for the team.

“The energy and wisdom he brings, and the bond he has with some of those guys, you could tell how excited they were the minute he walked through the gym doors,” Mihub said.

Keynan Middleton (left) and Putnam head coach Ali Mihub 

A 2012 Milwaukie High School graduate, Middleton starred in basketball and baseball for the Mustangs. He helped lead Milwaukie to the 5A title game on the hardwood as a senior.

Middleton played college baseball at Lane Community College and was selected in the third round of the 2013 MLB draft by the Los Angeles Angels. He made it to the major leagues in 2017 and has stuck around ever since, also playing for the Seattle Mariners, Arizona Diamondbacks, Chicago White Sox and New York Yankees.

While grinding through the minor leagues, Middleton began coaching basketball at his alma mater during the baseball offseason. He made the move to Putnam after Mihub was promoted from assistant to head coach after the 2022-23 season. 

“When I heard that he got the job, he asked me if I’d come over,” said Middleton, who has known Mihub since their AAU basketball days. “It’s been a great opportunity. From the second I heard that I’d be able to have the kids in the weight room and do skills with them in the morning, I knew it was going to be a great opportunity for me. I was happy he brought me along.”

Mihub felt Middleton was a perfect fit for a rebuilding program that hadn’t won a postseason game since 2002.

“Just the amount of information he has from getting to a high level, I think he was really able to feed the kids what it takes to get to that point,” Mihub said. “He’s able to tell kids the mindset they need to have and how they can’t take things for granted. He’s probably seen some incredible stories of people who didn’t think they were going to get to (MLB), make it. So, to have him tell the kids that you have to bring it every day, you can’t take a day off, and just talk about the level at which you need to consistently compete has been awesome.”

The Kingsmen entered the season with six seniors and star junior wing Jaiden Pickett, who has known Middleton his whole life. Pickett’s mom is Middleton’s godmother.

Putnam junior Jaiden Pickett (right) (photo by Leon Neuschwander) 

“He’s been a part of our family, and I’m glad he decided to come over this year,” Pickett said. “He’s like a brother to us. He helped us in the morning workouts we did with him every week. He was a big part of our group and our success.”

Added senior Lennon Greenleaf: “He’s a really good coach. He’s got a balance of being one of us, cool with us, while also bringing discipline and being hard on us when he needs to.”

Having a strong relationship with Pickett helped Middleton develop a quick bond with his new team.

“My little brother who graduated from Milwaukie last year also knows most of these kids and played against most of these kids,” Middleton added. “So, making that connection was easy. For them to trust me, that was 100 percent on them. They came, they showed up, they trusted what I was doing, they trusted what all of us were doing. I couldn’t ask them for any more.” 

Middleton said he plans to continue coaching for Putnam next season. Pickett will be the team’s lone returning starter, but the Kingsmen have a promising group of freshmen and sophomores who just witnessed what is required to be successful.

“I think this year is going to give a lot of inspiration and lay the blueprint for the younger groups,” Mihub said. “They got to see how much work it takes in the offseason, the morning workouts and the level at which you need to practice.”

Added Middleton: “I think everybody is really proud of these kids. To be where they were at the last few years and where the program’s been the last couple of decades … to come out and do what they did is something special. I think it says a lot about the group and how close they are.”

Middleton’s brief return to coaching ended over the weekend.

Just hours after Putnam’s loss to Woodburn in the third-place game, Middleton was on a plane back to Florida. He rejoined the Cardinals on Sunday and was ready for duty by Monday’s Grapefruit League game against the Washington Nationals.

The Cardinals finished 71-91 last year after winning the National League Central Division title in 2022, but Middleton has liked what he’s seen from the group so far.

“It seems like they’ve brought a lot of veterans in,” Middleton said. “They had a pretty young core last year, so they brought a lot of older guys in like me to show people the right way to do stuff.

“Camp’s been cool so far. We have a lot of meetings, we have a lot of structure, and that’s all I can ask for.”

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